76375-66-1

Upstream product

• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 2397-26-4 N,N-dimethyl(chlorophenylmethylene)ammonium chloride 
• 100-39-0 benzyl bromide 
• 620-05-3 iodomethylbenzene 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 611-74-5 N,N-dimethylbenzamide 
• 14155-23-8 methyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 709-50-2 methyl beta-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 77449-14-0 (3aR,4S,5aR,8R,9aR,9bS)-2,2-Dibutyl-4-methoxy-8-phenyl-hexahydro-1,3,5,7,9-pentaoxa-2-stanna-cyclopenta[a]naphthalene 
• 910660-96-7 Bis-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-thiocarbamic acid O-((2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl) ester 
• 473711-72-7 methyl 2,3-di-O-trimethylsilyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 100-44-7 benzyl chloride 
• 100-52-7 benzaldehyde 

Downstream Products

• 116391-14-1 methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-D-rhamnopyranosyl)-α-D-glucopyranoside 
• 58341-56-3 Methyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 157809-94-4 (4aR,6S,7S,8aR)-7-Benzyloxy-6-methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one 
• 192636-99-0 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-(3-2H)allopyranoside 
• 192637-07-3 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-(2-2H)allopyranoside 
• 192637-01-7 methyl 2-O-benzyl-4,6-O-benzylidene-3-O-triflyl-α-D-(3-2H)allopyranoside 
• 192637-09-5 methyl 2-O-benzyl-4,6-O-benzylidene-3-O-triflyl-α-D-(2-2H)allopyranoside 
• 192637-03-9 [2-2H] 2-O-benzyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose 
• 58769-74-7 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glucopyranose 
• 100759-92-0 3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranose 
• 72984-63-5 1,3,4,6-tetra-O-acetyl-2-O-benzyl-α- and β-D-glucopyranose 
• 55735-75-6 methyl 3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranoside 
• 109010-30-2 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose 
• 1379442-45-1 methyl 2-O-benzyl-4-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-α-D-glucopyranoside 

Relevant academic research and scientific papers

Anti-dengue, cytotoxicity, antifungal, and in silico study of the newly synthesized 3-O-Phospo-α-D-glucopyranuronic acid compound

The aim of the current study was to synthesize new bioactive compounds and evaluate their therapeutic relevance.The chemical structure of compound 7 (methyl 3-O-phospo-D-glucopyranuronic acid was elucidated by physical and advance spectral technique. Also, this compound was assessed for various in vitro biological screening. The results showed that compound 7 has promising antifungal activity against selected fungal strains. Computational study was also carried out to find antimalarial efficacy of the synthesized compounds. Compounds (2-7) were tested for cytotoxicity by MTT assay, and no considerable cytotoxicity was observed.Molecular docking studywas performed to predict the bindingmodes of newcompound (7).Thedocking results revealed that the compound has strong attraction towards the target protein, as characterized by good bonding networks. On the basis of the acquired results, it can be predicted that compound (7) might show good inhibitory activity against dengue envelope protein.

Carbohydrate-Derived Metal-Chelator-Triggered Lipids for Liposomal Drug Delivery

Liposomes are versatile three-dimensional, biomaterial-based frameworks that can spatially enclose a variety of organic and inorganic biomaterials for advanced targeted-delivery applications. Implementation of external-stimuli-controlled release of their cargo will significantly augment their wide application for liposomal drug delivery. This paper presents the synthesis of a carbohydrate-derived lipid, capable of changing its conformation depending on the presence of Zn2+: an active state in the presence of Zn2+ ions and back to an inactive state in the absence of Zn2+ or when exposed to Na2EDTA, a metal chelator with high affinity for Zn2+ ions. This is the first report of a lipid triggered by the presence of a metal chelator. Total internal reflection fluorescence microscopy and a single-liposome study showed that it indeed was possible for the lipid to be incorporated into the bilayer of stable liposomes that remained leakage-free for the fluorescent cargo of the liposomes. On addition of EDTA to the liposomes, their fluorescent cargo could be released as a result of the membrane-incorporated lipids undergoing a conformational change.

Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides

A phenylselenoglycosylation reaction of glycal derivatives mediated by diphenyl diselenide and phenyliodine(III) bis(trifluoroacetate) under mild conditions is described. Stereoselective glycosylation has been achieved by installing fused carbonate on those glycals. 3,4-O-Carbonate galactals and 2,3-O-carbonate 2-hydroxyglucals are converted into corresponding glycosides in good yields with excellent β-selectivity, resulting in 2-phenylseleno-2-deoxy-β-galactosides and 2-phenylseleno-β-mannosides which are good precursors of 2-deoxy-β-galactosides and β-mannosides, respectively.

A General Approach to O-Sulfation by a Sulfur(VI) Fluoride Exchange Reaction

O-sulfation is an important chemical code widely existing in bioactive molecules, but the scalable and facile synthesis of complex bioactive molecules carrying O-sulfates remains challenging. Reported here is a general approach to O-sulfation by the sulfur(VI) fluoride exchange (SuFEx) reaction between aryl fluorosulfates and silylated hydroxy groups. Efficient sulfate diester formation was achieved through systematic optimization of the electronic properties of aryl fluorosulfates. The versatility of this O-sulfation strategy was demonstrated in the scalable syntheses of a variety of complex molecules carrying sulfate diesters at various positions, including monosaccharides, disaccharides, an amino acid, and a steroid. Selective hydrolytic and hydrogenolytic removal of the aryl masking groups from sulfate diesters yielded the corresponding O-sulfate products in excellent yields. This strategy provides a powerful tool for the synthesis of O-sulfate bioactive compounds.

To acetyl cedilanid glucose modified compound liposomes and the use thereof (by machine translation)

The invention discloses a de-acetyl cedilanid glucose modified compound liposome and its application. Mainly from the cedilanid glucose-based reconstruction, to glucose and 2 - amino glucose as raw material for some molecular modification with the end of the digoxin 3 - hydroxyl at the delivery into connected to acetyl cedilanid glucose-based modified product, in active under the guide of the choose to conform with the requirements of the molecule. By synthesis to acetylation cedilanid glucose modified compounds (2 - O - benzyl - β - D - glucopyranoside - acetyl cedilanid and the like), so as to enhance the anti-cancer effect of such compounds, improve the strength of the titer, prolong the half-life, at the same time the modified compound preparation into the liposome, improve the targeting [...], reduce cardiac toxicity. (by machine translation)

Chemoenzymatic Synthesis of Advanced Intermediates for Formal Total Syntheses of Tetrodotoxin

Advanced intermediates for the syntheses of tetrodotoxin reported by the groups of Fukuyama, Alonso, and Sato were prepared. Key steps include the toluene dioxygenase mediated dihydroxylation of either iodobenzene or benzyl acetate. The resulting diene diols were transformed into Fukuyama's intermediate in six steps, into Alonso's intermediate in nine steps, and into Sato's intermediate in ten steps.

Synthesis of MeON-neoglycosides of digoxigenin with 6-deoxy- and 2,6-dideoxy-D-glucose derivatives and their anticancer activity

Cardiac glycosides show anticancer activities and their deoxy-sugar chains are vital for their anticancer effects. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and get more potent anticancer agents, a series of MeON-neoglycosides of digoxigenin was synthesized and evaluated. First, ten 6-deoxy- and 2,6-dideoxy-D-glucopyranosyl donors were synthesized starting from methyl α-D-glucopyranoside and 2-deoxy-D-glucose. Meanwhile, the digoxigenin was obtained by acidic hydrolysis of commercially available digoxin as glycosyl acceptor. Then, a 22-member MeON-neoglycoside library of digoxigenin was successfully synthesized by neoglycosylation method. Finally, the induction of Nur77 expression and its translocation from the nucleus to cytoplasm together with cytotoxicity of these MeON-neoglycosides were evaluated. The SAR analysis revealed that C3 glycosylation is required for their induction of Nur77 expression. Moreover, some MeON-neoglycosides (2b and 8b) could significant induce the expression of Nur77 and its translocation from the nucleus to cytoplasm. However, these compounds showed no inhibitory effects on the proliferation of cancer cells, suggesting that they may not induce apoptosis of NIH-H460 cancer cells and their underlying potential and application toward cancer cells deserves future study.

Regioselective alkylation of carbohydrates and diols: A cheaper iron catalyst, new applications and mechanism

As an extension of our previous research on the regioselective protection of carbohydrates and diols, we developed an iron catalyst, Fe(dibm)3 (dibm = diisobutyrylmethane), which has an unusually broad catalytic scope in the selective monoalkyl

Co2(CO)6-propargyl cation mediates glycosylation reaction by using thioglycoside

We discovered that the cobalt-propargyl cation can mediate the glycosylation reaction by activating the thioglycoside donor. The glyco-oxacarbenium cation was formed by transferring the thio-aglycone to the cobalt-propargyl cation that was generated from the cobalt-propargylated acceptor in situ via the activating with Lewis acid. The reactivity of the donor (Armed or dis-armed) and the amount of the Lewis acid control the releasing rate of the cobalt-propargyl group.

Synthesis and binding affinity analysis of α1-2- and α1-6-O/S-linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors

The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards α1-2- and α1-6-linked dimannosides with S- or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrene-mediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the α1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the α1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the α1-2-analog displayed very similar binding compared to the O-linked structure.